Jimmy Ollson
Jimmy Olsson

Jimmy Olsson, who carries himself with just as much consideration as he wears his neatly tailored clothes, is sitting on a gray couch in the back of the Todd Snyder x Champion store on Elizabeth Street in New York City’s NoLita neighborhood surveying a small, but important, part of an empire he has been steadily building for more than three years. The space, dubbed the “City Gym” combines the utilitarian elements of a locker room (exposed metal racks, bolted into the wall; broken-in lockers), with the ambiance of a private members club, with black-and-white photographs, and furniture sourced from ABC Carpet and Home. Originally intended as a short-term pop-up last November, this space will remain open at least through June and features the full range of Todd Snyder’s Champion collaboration as well as carefully sourced pieces from complementary brands such as Shinola and Faribault. Olsson is the president and CEO of Todd Snyder as well as Tailgate Clothing—Snyder is the creative director of both, and the two men have developed the kind of symbiotic working relationship that is the envy of many in the men’s fashion business. Their collaboration has created spaces like "City Gym' and wearable collections that cut a new path in men’s fashion, including pieces like this soft, lived-in crew neck sweatshirt, sitting in front of me on a quilted bench (you can buy the bench, like the other furniture in the store by contacting ABC).

“It’s all about quality,” says Olsson who is clearly (and justifiably), proud of the careful curation of the space. “We want that, right there, to be your favorite sweatshirt. I wear that one: I have five colors of it, and I wear it almost everyday. And I do that because of the quality: the fit’s right, and it’s great fabric. And that’s our focus when we’re doing everything. And yes our T-shirts are $60, which is a lot, but it’s the greatest T-shirt you’ll buy.” Of course, he would say that. He’s the CEO. But, months before I was assigned this piece I wandered into this store and bought a pair of sweatpants (don’t judge), and they are, it has to be said, the best sweatpants I have ever owned.

This belief in the quality of their product, and their understanding of the buying habits of the modern guy have set Olsson and Snyder up for the best kind of success. The kind that comes from an innate understanding of their customer, an unfailing, laser-sighted focus on authenticity, and the kind that isn’t going anywhere soon. Put simply, they’re playing the long game. “We’re not trying to build some flash-in-the-pan brand,” Olsson says. “This is a long-term thing for us, and we want to make sure we get it right.” It’s an approach that has been honed over almost a quarter of a century working in fashion merchandising starting with his first mentor, a man whose very name is synonymous with innovation in retail: Mickey Drexler.

It was Olsson’s first proper job, working at Gap’s global headquarters in San Francisco, where he started in Merchandising, where Mickey was then CEO. “We all say in the business that if you worked for Mickey then you went to the Harvard School of Merchandising,” Snyder says, with a smile. “There are very few people like him. Mickey was a great teacher, a great mentor, and he really laid the foundation of all of us and his mantra was: ‘It’s all about the product.’ He still says it. Even if you listen to any of the investor calls or interviews with him: It’s all about the product. Todd and I look at our business today from those learnings.”

It was at the Gap that Olsson’s path first crossed Snyder’s, who was a designer of men’s sportswear at the company. “Back then it was about being smart enough to be focused on your design team,” Olsson says. “And that’s why Todd and I work so well together: Todd was my designer and I was his merchant, so he would say, ‘Hey, this is what’s coming next,’ and we’d have discussions about making sure we’re protecting our existing business but also building for what was next.” After stints at Polo Ralph Lauren and J.Crew Snyder returned to the Gap as Director of Menswear in 2000, but left in 2004 to become VP of Menswear at J.Crew, launching numerous heritage brand collaborations and the successful Liquor Store concept in TriBeCa. Olsson, meanwhile, took on senior merchandising positions at Coach and Rip Curl, where he was president, CEO, and, to hear him tell it—pretty stoked. “Part of the interview was I had to surf,” says Olsson who, not coincidentally, is an avid surfer. After three years in Laguna Beach, Olsson went to Martin + Osa, a brand launched by American Eagle.  After 5 years at Martin +Osa, Olsson joined the Wal-Mart NY Apparel office. “We built brands internally,” he says. “The leadership, the customer focus, they were amazing at it, and I really enjoyed the job.”

Two years later, the pair crossed paths, shortly after Snyder had relaunched Tailgate, a T-shirt company that Snyder started in his father’s basement in Iowa, and his own namesake line of casual classics, born from the literal and figurative heartland of American heritage but developed, as is Snyder’s trademark, with the discerning, modern gentleman in mind. They don’t seem to have paused for breath since. “We both left our ‘real’ jobs, as I call them—our corporate jobs—to do this,” says Olsson, who despite usually staying on the sidelines and ushering Snyder onto the stage is a poised interview. “It goes back to trust, but it also goes back one another. Todd will challenge me on the business: he has a very strong right brain, but a really strong left brain as well. The other day we went back and looked at all of our fits together because I brought a lot of the stuff home and it didn’t fit me: we have an open dialogue as partners, and with our team. We have an amazing team, and there’s constant feedback.”

Followers of Joe's Blackbook would be interested to hear about your hiring process. “The main thing for me,” he says, “If I’m interviewing you for Todd Snyder, you should know everything about our business—where we sell it; you should have seen it, been in the stores. You have to be a student of our business. If someone comes in and hasn’t done their homework, they likely won’t get hired. Where we’ve always made hires is when someone comes in and has an idea or can add value right way. A lot of people coast in and want the job. Then there’s people who come in and their Ts are crossed and their Is are dotted and they’re like, ‘Hey, I saw this white space for you—you guys could have a much bigger woven presence.’” For Olsson, a point of view is key. And when I tell him that it isn’t always that easy to point out to a CEO areas their company could improve, he counters: “The interviewer should ask you. ‘Have you shopped on our site?’ Would be the first question I would ask if I was looking for someone to potentially run ecommerce for us. If that person hasn’t shopped our site, doesn’t have feedback, or can’t provide opportunities—I wouldn’t hire them, even if they were great technically. I would want them to have a point of view.”

Such candor distinguishes Olsson as a businessman and the professional environments he creates with Snyder (the Todd Snyder team is currently only eight people but growing; Tailgate is around 20). “It’s rigorous, but it’s not ruthless,” Olsson says of the office culture. “We’re not there to motivate people: Todd and I love what we do, we’re fortunate that our job is something we enjoy, and we want the people we bring in to be the same. And you have to be able to keep going. You never get downtime in fashion. It’s ongoing and you have to be able to keep up.”

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